(3S,5S)-5-((4R,5R)-2,2-dimethyl-5-((triethylsilyl)oxy)-1,3-dioxan-4-yl)-5-methoxy-3-methylpentan-1-ol | 1310357-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5S)-5-((4R,5R)-2,2-dimethyl-5-((triethylsilyl)oxy)-1,3-dioxan-4-yl)-5-methoxy-3-methylpentan-1-ol
• CAS: 1310357-45-9
• 化学式: C₁₉H₄₀O₅Si
• 分子量: 376.609
• InChiKey: KUIIAYVFKIUEKJ-WNRNVDISSA-N

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-((4R,5R)-2,2-dimethyl-5-((triethylsilyl)oxy)-1,3-dioxan-4-yl)-5-methoxy-3-methylpentan-1-ol 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到(((4R,5R)-4-((1S,3R)-5-bromo-1-methoxy-3-methylpentyl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane
  参考文献：
  名称：

  Synthesis of Key Fragments of Leiodelide A

  摘要：

  The synthesis of all key fragments of the marine macrolide lelodelide A is described. The polyoxygenated northern subunit is derived from D-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of lelodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

  DOI：

  10.1021/ol201183f
• 作为产物：
  描述：

  (((4R,5R)-4-((1S)-5-(benzyloxy)-1-methoxy-3-methylpentyl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 6.0h， 以223 mg的产率得到(3R,5S)-5-((4R,5R)-2,2-dimethyl-5-((triethylsilyl)oxy)-1,3-dioxan-4-yl)-5-methoxy-3-methylpentan-1-ol
  参考文献：
  名称：

  Synthesis of Key Fragments of Leiodelide A

  摘要：

  The synthesis of all key fragments of the marine macrolide lelodelide A is described. The polyoxygenated northern subunit is derived from D-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of lelodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

  DOI：

  10.1021/ol201183f